2-(Ethoxycarbonyl)-3-(trifluoromethyl)-4-ethylpyrrole | 127074-08-2

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡咯
• 英文名称: 2-(Ethoxycarbonyl)-3-(trifluoromethyl)-4-ethylpyrrole
• 英文别名: 2-ethoxycarbonyl-3-trifluoromethyl-4-ethylpyrrol；ethyl 4-ethyl-3-(trifluoromethyl)-1H-pyrrole-2-carboxylate
• CAS: 127074-08-2
• 化学式: C₁₀H₁₂F₃NO₂
• 分子量: 235.206
• InChiKey: CYVRZFWPMXTLLK-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.9
• 重原子数：
  16
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  42.1
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  二甲醇缩甲醛 、 2-(Ethoxycarbonyl)-3-(trifluoromethyl)-4-ethylpyrrole 在 三氟化硼乙醚 作用下， 以 二氯甲烷 为溶剂， 反应 35.0h， 以88.5%的产率得到5,5'-Bis(ethoxycarbonyl)-3,3'-(trifluoromethyl)-4,4'-diethylpyrromethane
  参考文献：
  名称：

  Nonionic Superbase-Promoted Synthesis of Oxazoles and Pyrroles: Facile Synthesis of Porphyrins and .alpha.-C-Acyl Amino Acid Esters

  摘要：

  The reaction of acyl chlorides or acid anhydrides with isocyanoacetates in the presence of the superior strong nonionic base P(MeNCH(2)CH(2))(3)N (1) gave oxazoles in 98-99% yield. Treatment of the oxazoles with HCl-MeOH gave alpha-C-acyl amino acid esters in 81-82% yield. The reaction of beta-acetoxy-alpha-nitroalkanes or nitroalkenes with isocyanoacetates in the presence of 1 gave pyrroles in 100% yield. The conjugate acid of 1 can be treated with KO-t-Bu to regenerate 1. Treatment of the pyrroles with LiAlH4, followed by PTSA-CH2(OMe)(2) and oxidation gave porphyrins in 65-69% yield. LiCl, which functions both as a strong nucleophile in the S(N)2 demethylation of the 5,5'-bis(methoxycarbonyl)-3,3',4,4'-tetramethyldipyrromethane 22a and as a Lewis acid in the electrophilic substitution cyclization of paraformaldehyde at dipyrromethane, facilitates the combination of four reactions into a one-pot synthesis of octaethylporphyrin in 67% yield from 22a.

  DOI：

  10.1021/jo00104a041
• 作为产物：
  描述：

  1,1,1-trifluoro-3-nitro-2-pentanol 在 硫酸 、 1,8-二氮杂双环[5.4.0]十一碳-7-烯 作用下， 以 四氢呋喃 为溶剂， 反应 12.0h， 生成 2-(Ethoxycarbonyl)-3-(trifluoromethyl)-4-ethylpyrrole
  参考文献：
  名称：

  三氟甲基化吡咯和卟啉的简便合成

  摘要：

  4-烷基-3-三氟甲基-2-吡咯甲酸酯（2）可通过三氟甲基化β-硝基乙酸酯（1）与异氰乙酸乙酯反应方便地制备。吡咯通过 2-（羟甲基）吡咯的四聚作用转化为相应的卟啉。

  DOI：

  10.1246/bcsj.62.3386

文献信息

• ONO, NOBORU;KAWAMURA, HISAYUKI;MARUYAMA, KAZUHIRO, BULL. CHEM. SOC. JAP., 62,(1989) N0, C. 3386-3388
  作者：ONO, NOBORU、KAWAMURA, HISAYUKI、MARUYAMA, KAZUHIRO

  DOI：——

  日期：——
• Nonionic Superbase-Promoted Synthesis of Oxazoles and Pyrroles: Facile Synthesis of Porphyrins and .alpha.-C-Acyl Amino Acid Esters
  作者：Jiansheng Tang、John G. Verkade

  DOI：10.1021/jo00104a041

  日期：1994.12

  The reaction of acyl chlorides or acid anhydrides with isocyanoacetates in the presence of the superior strong nonionic base P(MeNCH(2)CH(2))(3)N (1) gave oxazoles in 98-99% yield. Treatment of the oxazoles with HCl-MeOH gave alpha-C-acyl amino acid esters in 81-82% yield. The reaction of beta-acetoxy-alpha-nitroalkanes or nitroalkenes with isocyanoacetates in the presence of 1 gave pyrroles in 100% yield. The conjugate acid of 1 can be treated with KO-t-Bu to regenerate 1. Treatment of the pyrroles with LiAlH4, followed by PTSA-CH2(OMe)(2) and oxidation gave porphyrins in 65-69% yield. LiCl, which functions both as a strong nucleophile in the S(N)2 demethylation of the 5,5'-bis(methoxycarbonyl)-3,3',4,4'-tetramethyldipyrromethane 22a and as a Lewis acid in the electrophilic substitution cyclization of paraformaldehyde at dipyrromethane, facilitates the combination of four reactions into a one-pot synthesis of octaethylporphyrin in 67% yield from 22a.
• A Convenient Synthesis of Trifluoromethylated Pyrroles and Porphyrins
  作者：Noboru Ono、Hisayuki Kawamura、Kazuhiro Maruyama

  DOI：10.1246/bcsj.62.3386

  日期：1989.10

  4-Alkyl-3-trifluoromethyl-2-pyrrolecarboxylic acid esters (2) were conveniently prepared by the reaction of trifluoromethylated β-nitro acetates (1) with ethyl isocyanoacetate. The pyrroles were converted into the corresponding porphyrins via tetramerization of 2-(hydroxymethyl)pyrroles.

  4-烷基-3-三氟甲基-2-吡咯甲酸酯（2）可通过三氟甲基化β-硝基乙酸酯（1）与异氰乙酸乙酯反应方便地制备。吡咯通过 2-（羟甲基）吡咯的四聚作用转化为相应的卟啉。